Dr Prantik Maity

We have developed an enantioselective, copper(I)-catalyzed addition of terminal
alkynes to racemic isochroman acetals. This method is one of the first transition-metalcatalyzed
approaches to enantioselective additions to prochiral oxocarbenium ions. In this
reaction, TMSOTf is used to form the oxocarbenium ion in situ under conditions
compatible with simultaneous formation of the chiral copper acetylide. By using a
bis(oxazoline) ligand, good yields and enantioselectivities are observed for a variety of
enantioenriched 1-alkynyl isochromans.

We have developed a nickel-catalyzed cross coupling of benzylic ammonium trifl
ates with aryl boronic acids to aff ord diarylmethanes and diarylethanes. This reaction
proceeds under mild reaction conditions and with exceptional functional group tolerance.
Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent
chirality transfer, off ering a new strategy for the synthesis of highly enantioenriched
diarylethanes from readily available chiral benzylic amines.